Hofmann-Löffler reaction

Hofmann-Löffler reaction

The Hofmann-Löffler reaction or Hofmann-Löffler-Freytag Reaction is an organic reaction is which a haloamine is converted to a cyclic amine such as a pyrrolidine with heat and an acid [cite journal
title = Ueber die Einwirkung des Broms in alkalischer Lösung auf die Amine (p )
author = August Wilhelm von Hofmann
journal = Berichte der deutschen chemischen Gesellschaft
volume = 16
issue = 1
pages = 558–560
year = 1883
url =
doi = 10.1002/cber.188301601120 ] [cite journal
title = Über eine neue Bildungsweise von N-alkylierten Pyrrolidinen
author = Karl Löffler, Curt Freytag
journal = Berichte der deutschen chemischen Gesellschaft
volume = 42
issue = 3
pages = 3427–3431
year = 1909
url =
doi = 10.1002/cber.19090420377 ] [JerryMarch]

An example is the synthesis of n-butylpyrrolidine [Organic Syntheses, Coll. Vol. 3, p.159 (1955); Vol. 25, p.14 (1945). http://www.orgsynth.org/orgsyn/pdfs/CV3P0159.pdf]

:

The reaction type is a radical substitution. In the first step the halogen atom migrates from nitrogen to a gamma or delta carbon position in a rearrangement reaction.

A conceptually related reaction is the Barton reaction.

References


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